(benzyl tri ethyl ammonium chloride) ..

To a stirred mixture of each of aromatic or heteroaromatic amines 1a-f (20 mmol), triethylorthoformate (10 mmol) in water (20 mL) was added cerium (IV) ammonium nitrate (10 mol%). The reaction mixture was stirred at room temperature (27˚C) for 10 - 40 minutes. For liquid amines a solid was formed, while for solid amines, they dissolved in the reaction medium and then resolidified forming the final product. The resulting solid was collected by filtration and recrystallized from ethanol to afford analytically pure samples 3a-h. Compounds 3a-f have been described previously [31-37] and were found identical with our samples synthesized by our protocol.

Ionic Liquid Based Systems for Aromatic Nitration

and and and and and and (2012)Efficient, rapid synthesis of bis(indolyl)methane using ethyl ammonium nitrate as an ionic liquid. RSC Advances, 02. pp. 3525-3529.

PART A REVERSIBLE REACTIONS - Doc Brown

A simple and rapid protocol has been developed for an efficient synthesis of bis(indolyl) methane in excellent yields using ethyl ammonium nitrate (EAN) as reusable ionic liquid at room temperature. The protocol involves an electrophilic substitution reaction of indoles with several aldehydes.